He picks me up and we head to dinner and I must say nigga had it going on. Nice light brown complexion, facial hair trimmed up tight, gray suit, didn�...�t look like he was in his 40s. So we get to the restaurant downtown and he asks for a booth so we can sit next to each other. He plays with my pussy under the table the whole time. After dinner we head down 95 to the casino for the show. Al B. Sure came on first. He was all right. Tony Tony Tony then came on. At some point I had my legs crossed. ‘Not really, but I have class now,’ she offered with a small smile, trying to avoid looking him up and down. ‘See you later, Cassie,’ he smiled back, his front tooth had a chip out of it. It was the first time Cassie had even seen a smile that large from Luke. ‘Uh, thanks, you know, for letting me intrude,’ she responded warmly. ‘Anytime.’ And his head bent back over his books, easy posture gone, closed off again. The diner was busy, even for a Friday. Pippa was largely ignoring her tables. She pulled a condom out of her back pocket,"Come on, lets fuck right here". She dropped her shorts, she wasn't wearing panties. I looked around, we were hidden by a blue plastic tarp, "Okay, okay" I said unzipping my jeans. Jessie didn't waste any time, she took the condom and placed it on the tip of my cock and rolled it down over the shaft with her mouth. Then her warm mouth enveloped my cock, she was breathing out of her nose and I could feel her hot breath tickle the hairs on my inner. Career, hobbies, familiarity; blame it on whatever. We were in a rut. So I was shocked as hell when she proposed that this year, the loser of the bet took it up the butt!! She had ALWAYS said that was off limits and there was no way I was ever going in the “Out Door”. But she made the stakes, and I knew my team had been winning everything so I went with it.Me? I am all man. And while I like it when Beth takes charge, taking a strapon up my butt was not on my bucket list. But I felt safe. I was.
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